Synthesis of Heterocyclic Compounds from Imine and Study of Chromatography Applications.

 

Marwa T. Khattar1, Dr. Nagham M. Aljamali2*, Dr. Kasim K. Alasadi3

1M. Sc. Researcher, Chem. Dept., College of Education, Univ. of  Kufa, Iraq.

2Assist. Prof., Chem. Dept., College of Education, Univ. of Kufa, Iraq.

3Assist. Prof., College of Science, Univ. of Kufa, Iraq

*Corresponding Author E-mail:dr.nagham_mj@yahoo.com

 

ABSTRACT:

The aim of this work, synthesis of heterocycles included more than one hetero atom like (N, S, O) to produce various cycles [3-8] membered ring. This work involved five parts, included synthesis of compounds [1-20] first part includes synthesis of three compounds [1,11,17] through reaction between 4-alimethyl amino benzaldehyde with different primary aromatic amines to give (schiff bases ), second part involved synthesis of compounds [2, 1218, 20] from reaction between schiff bases with (maliec anhydride m, cystiene, 3,5dinitro salcylic acid , 0-thiol  benzoic acid, alanine ) to give (oxazepine, imidazolidine, oxazine ) third part synthesis of diazepine compounds [3-5] from reaction between oxazepine with (hydro guandine, thiosimecarbazide, thiourea ) four part involved synthesis of compounds [6-10] from reaction between  Diazepine with (di chloro methane, benzoic acid, oxalic acid, di chloro ethane ) to give (three, four, five) rings, five part involved of compounds [13-16] from reaction between five membered with (phthalic anhydride, malic anhydride, oxalic acid, dichloro ethane) to give (three, five, six, eight), six part include: study of  chromatography.

The structure of these compounds were characterized by (H.NMR, FI.IR, C.H.N) -techniques and their melting points, then study of chromatography behavior.

                                                                            

KEYWORDS: Oxazepine, diazepine, maziridine, schiff base, melamine, four membered, eight membered

 


INTRODUCTION:

Heterocyclic compounds used to develop of biological or medicinal interest to chemists (1). The compounds generally consist of (5,6,7-membered) saturated at unsaturated cycles of more than one hetero atom which may be similar or dissimilar(2). The aromatic-hetero cyclic polymers are one of versatile and widely utilized class of organic polymers, they are used in several applications(3) . oxazepine refers to any seven-membered ring containing au oxygen and  nitrogen atom(4), synthesis of these compounds in this work is a class of  pericyclic reaction which is classified as a (5+2=7), implying5-atom component plus 2- atom component leading to 7- membered cyring(5). Oxazepinederivative is used as an antibiotic, enzyme inhibitor, pharmacological interest (6) and have dical and biological important(7).

 

Chemical compounds built on a diazepines fold have recently emerged as potent inhibitors of theacetyllysine binding activity of bromodomain-containing proteins, which is required for gene transcriptional activation in cancer and inflammation(8).  Diazepine derivatives are used as tranquilizers, anticonvulsant, anxiolytic, analgesics, sedatives, anti depressives and hypnotic agents. Diazepine continues. To be challenging end ever in synthetic organic chemistry(9) tetrazoles they are arowatic five membered ring containing four nitrogen atoms(10) Tetrazoles have been found to exhibit an exhibit antibacterial, antifungal, antihistamine and anti-inflammatory properties(11). Triazolesconntries an important class of organic compounds with divers agricultural, industrial and biological activities including, sedative, anti-convulsant-inflammatory(12), Literature survey reveals that 2-oxo-azetidines have shown various biological activities along with antimicrobial activity. In view of these findings some 2-oxo-azetidine derivatives of isoniazid have been synthesized and evaluated for anti-bacterial, antifungal and anti-tubercular activity (13). 4-oxo-azetidines are 4-membered cyclic amides derived from schiff bases which


contain B-lactam unit as an essential structure feature of its molecule (14). We have used schiff base condensation as the ring-closing step to synthesis oxazepine, diazepine, thio compound, the hetero atoms in there structure such as (S,N,O) explain variety of applications, antitumor, in the biological engineering and in other field of their specific structure(15). Schiff bases are anti-chemical good for some types of bacteria and fungi (16). Schiff base posses antituberior and anticancer activity(17) Gas chromatography (c-c) analysis of basic organic compounds (e.g. amines, basic drugs and azo dyes)is a challenge to the analyst, especially when the compounds are at low concentration(18) and these parathion mechanism depend on the selective phase, rate of carrier gas, temperature column(19) this technique is used to separate the numerous compounds, particularly  organic compounds such as alcoholsand hydrocarbons aolastarate ketones and, Aldehyde etc(20) 

 

Experimental Apparatus:-

All chemicals used (purity 99.98%), FT.IR-spectra: were recorded on Shimadzu 8300, KBr-disc, HNMR-spectra were recorded on Varian 300 MHZ spectrometer using TMS as an internal standard and elemental analysis (C.H.N)-elemental (Analyses system GmbH)-measurements were made at Department of Chemistry, Kashan University. Iran. The melting points were determined in open capillary tubes by electro thermal 9300 LTD, U.K.                                   

 

Synthesis of Compounds [1,2]

A mixture of 4- nitro aniline (0,0 1mole) and 4-dimethyl amino benzaldehyde (0,01 mole) in the presence of absolute ethanol with drops of glacial acetic acid and reflux for (2h), the precipitate was filtered and dried with recrystallized to yield (86%) of compound [I], which (0.01mole) reacted with (0.01mole) of maleic anhydride respectively in presence of dry benzene with refluxing for(4h), the precipitates filtered, recrystallized from ethanol to produce(88%) of compound[2].                                                                                              

 

Synthesis of Compounds[3-5]

A mixture of(0.01mole) of compound [2] with(o.o1mole) of one of(hydro guandine, thiosemicarbazide, thiourea) were refluxed in presence of dry benzene for (4h), the precipitates filtered, recystallized from dry benzene to produce(80,82  and 180)% of compound[3],compound[4] and compound[5], respectively.                                         

 

Synthesis of Compounds[6,7]

A mixture of (0,001 mole) of (dichloromethyl ) in the presence of KOH in absolute ethanol with drops of glacial acetic and reflux for (42h), (0,001 mole) of (benzoic acid) in the presence of (4N) hydro chloric acid and reflux for (36h), the precipitate was filtered and dried with recrystallized to yield(81,85)% of compound[6], compound[7], respectively.

 

Synthesis of Compound[8]

The reaction of compound[5] (0.01 mole) with (dichloro ethane) (0.01 mole) in the presence of KOH  in absolute ethanol for (3h), resulted in the formation (82%) of compound [8]

 

Synthesis of Compounds[9-10]

Ethanolic mixture of(0.01 mole) of compound[4] with(0.01 mole) of oxalic acid and (0.001mole) of dichloro methane to were refluxed for (4h) yield(84,85)% of compound[9] and compound[10]  respectively.

 

Synthesis of Compounds[11-14]

A mixture of (0.01 mole) of melamine with (o.o1 mole) of 4-dimethyl benzaldehyde in the presence of absolute ethanol with drops of glacial acetic acid and reflux for (4h), the precipitate was filtered and dried with recrystallised to yield (83%) of compound[11] which(0.01 mole) with (0.01 mole) of cystein respectively in presence of dry benzene with refluxing for (7h) the precipitate was filtered and dried with recrystallized to yield (80%) of compound[12], which (0.001 mole) with one of (0.001 mole) of (phthalic an hydride) in the presence of acetone with reflux for (4h) (0.003 mole) of (maliec acid) in the presence of absolute ethanol with droups of glacial acetic acid with reflux for(7h), The precipitates filtered, recrystallized to give (80,80) %  of compound[13], compound[14] respectively.

 

Synthesis of Compounds[15,16]

(1 mole) of compound [13] with (2mole) of one of (oxalic acid, dichlorechane) were refluxed in presence of Ethanol and presence of  K2CO3 for (7-8h), the precipitate was filtered and dried with recrystallized resulted in the formation (80,80)% of compound[15], compound[16] respectively.             

 

Synthesis of Compounds[17-20]

A mixture of(0.03 mole) of 4-dimethylaminopemzaldehyd, with(0.01 mole) of melamine in the presence of absolute ethanol with drops of glacial acetic acid and reflux for (4h), the precipitate was filtered and dried with recrystallized to yield(82%) of compound [17], which of one (0.03 mole) of (3,5-dinitrosakylicacid, (0.004 mole) of o-thiol benzoic acid and alanine) were refluxed in presence of dry benzene for (9h), the precipitate was filtered and dried with recrystallized to yield (80,82,80)% of compound [18], compound[19] and compound[20], respectively.


 

Scheme (1):Preparation of compounds [1-10]

 

 


Scheme (2):Preparation of compounds [11-20]

 

 


Analysis of Compounds [2, 3, 4, 5, 9 and Mixture] by Gas Chromatography:

Preparation of diluted  solutions (( concentration of 1ppm for vehicles)) of compounds [2, 3, 4, 5,9  and  Mixture] after dissolved with ethanol was also attended by a mixture of compounds which prepared by mixing 10ml of each solution individually after shaking continuous., injected models by using a syringe(Hamilton) with a capacity of 10ml individually and then injected the mixture, and then install the measurement conditions through the use of nitrogen a gas flow of 25ml/min bus speeds and injection temperature was 25Cº degrees higher than the temperature separation column and then use a flame ionization detector is 50Cº higher than the temperatures of the column either column temperature programmed gradual increase of (90-160)Cº, taking into consideration the maximum temperature to avoid damage to the column. All data are shown in Table (1) and figures (11-16).

 

RESULTS AND DISCUSSION:

All synthesized compounds [1-20] were characterized by FT. IR- spectra, (C.H.N)- analysis, melting points and some of  them by H.NMR-spectra]. FT.IR-spectra showed appearance absorption bends at (1604) cm-1 due to (CH=N) imine group, absorption band at (1350) cm-1 due to          (C-NO2) nitro group, absorption bends at (1298)cm-1 due to    (-N(CH3)2) dimethyl amine in compound [A1]. Appearance of absorption band at (1689)cm-1 due to carbonyl group (CO) lactam  (CO-N), absorption band at (1714)cm-1 due to carbonyl group (CO) of lactone (CO-O), absorption band at (2968)cm-1 due to (C-H) aliphatic, absorption band at (1408, 1284)cm-1 due to   (C-NO2) nitro group and (N(CH3)2) in compound [A2]. Appearance of absorption band at (1691, 1691, 1698)cm-1 due to (CO-N) lactam, absorption band at (3367, 3425, 3201, 3294, 3333, 3419)cm-1 due to NH2, absorption band at (3041, 3100, 3030)cm-1 due to (CH=CH) alkene, absorption band at (2929, 2933, 2999)cm-1 due to (C-H) aliphatic, absorption band at (1284, 1250, 1298)cm-1 due to (N(CH3)2) in compounds [A3, A4, A5], absorption band at (1390, 1346)cm-1 due to (C-NO2) nitro group in compounds [A3, A5], absorption band at (815)cm-1 due to   (C=S) in compound [A5]. Appearance of absorption band at (1680, 1689)cm-1 due to (CO-N) of lactam, absorption band at (1608, 1606)cm-1 due to (C=N) indo cycle of lactam, absorption band at (2910, 2929)cm-1 due to (C-O) aliphatic, absorption band at (1355, 1384)cm-1 due to (C-NO2), absorption band at (1230, 1250)cm-1 due to (N(CH3)2), absorption band at (3030, 3061)cm-1 due to(CH=CH), in compound [A, A7], absorption band at (3282) cm-1 due to (NH) in compound [A6]. Appearance of absorption band at (1699)cm-1 due to (CO-N) of lactam, absorption band at (3009)cm-1 due to (CH=CH) of alkene, absorption band at (2897)cm-1 due to (C-H) aliphatic, absorption band at (1380)cm-1 due to (C-NO2) nitro group, absorption band (1280)cm-1 due to (N(CH3)2), absorption band at (798)cm-1 due to (C=S) in compound [A8].  Appearance of absorption band at (1672, 1689)cm-1 due to (CO-N)of amide, absorption band at (3304, 3321)cm-1 due to (NH) of amide, absorption band at (3059, 3089)cm-1 due to (CH=CH) of alkene, absorption band at (1220, 1284)cm-1 due           (N(CH3)2) in compounds [A9, A10]. Appearance of absorption band at (1618)cm-1 due to (-CH=N-) of imine group, absorption band at (1608)cm-1 due to (C=N) of indo cycle of melamine, absorption band at (3435,(3435, 3421))cm-1 due to (NH2) of amine, absorption band at (1240)cm-1 due to (N(CH3)2) in compound [A11], which disappeared and other bands are appear at (1670)cm-1 due to (CO-N) of amide and two bands at (1598, 2362)cm-1 due to (C=N) of indo cycle of melamine, (SH) and band at (2972)cm-1 due to (C-H) aliphatic, absorption band at (3230, 3365)cm-1 due to (NH2) and band at (2286)cm-1 in compound [A12]. Appearance of absorption band at (1695, 1664)cm-1 due to (CO-N) of amide, absorption band at (1600)cm-1 due to (C=N) of indo cycle of melamine, absorption band at (2960, 2922)cm-1 due to (C-H) aliphatic, absorption band at (1246, 1240)cm-1 due to (N(CH3)2) in compounds [A13, A14] and band at (2362)cm-1 due to (SH) and band at (3340, 3281)cm-1 due to (NH2) in compound [A13] and band at (1365)cm-1 due to (CH2-S) in compound [A14]. Appearance of absorption band at (1681, 1684)cm-1 due to (CO-N) of  lactam , absorption band at (1604)cm-1 due to (C=N) indo cycle of melamine and bands at (2939, 2904)cm-1 due to (C-H) aliphatic and bands at (1398, 1320)cm-1 due to (CH2-S) and bands at (1298, 1294)cm-1 due to (N(CH3)2) in compounds [A15, A16]. Appearance of absorption bands at (1624, 1588, 1298)cm-1 due to (CH=N) of imine group, (C=N) of indo cycle of melamine and (N(CH3)2) respectively in compound [A17]. Appearance of absorption band at (1688, 1680, 1662)cm-1 due to (CO-N) of amide absorption band at (1595, 1608, 1597)cm-1 due to (C=N) of indo cycle of melamine and bands at (1255, 1230, 1234)cm-1 due to (N(CH3)2) in compounds [A18, A19, A20], absorption band at (1431)cm-1 due to (CH-S) in compound [A19], absorption bands at (2904, 1371, 1165)cm-1 due to (CH) aliphatic, (C-NO2) and (C-O-C) ether group in compound [A18]. Absorption band at (2908, 3230)cm-1 due to (C-H) aliphatic and (NH) amine group in compound [20]., all data are shown in Table (2) and figures (1-5).


 

 


Table (1). Specification Used Capillary Columns

Polarity

Max operatory Temp.(M.O.T)

Column dimension

Formula

Composition

Liquid phase

Low  polar

(300)

0.25mm I.D 0.12 Mm d.f

 

2,3-di-o-propionyl-6-t-butylsilyl derivative of ᵞ-cyclodextrin phase

DP5-25

Moderately polar

 -20C؛-280C؛-(300)C؛

0.25mm I.D 0.25Mm d. f

14%Cyanopropyl phenyl poly siloxane

FS-BP10


1H.NMR-Spectrum:

H.NMR-Spectrum of compounds showed signal at δ(8.66) for one proton of  azomethine group (-CH=N-) , sign at and (2.99) for protons of dimethyl amine (N(CH3)2), two signal at and (6.74-7.66) for protons of phenyl rings in compound [A1]. Signal at (9.63) for proton of (O-CH-N) of oxazepine ring, signal at (6.06) proton of (CO-CH=CH-CO) of alkene in oxazepine ring, signal at and (2.85) for protons of (N(CH3)2), two signal at  and (6.74-7.66)protons of phenyl rings in compound [A2]. Signal at and (2.99) protons of (N(CH3)2), signal at and (2.47) of proton of diazepine ring, doublet signal and (2.25) protons of alkene (CO-CH=CH-CO), two signal at and (6.74- 7.65) for protons of phenyl rings, signal at and (9.63/ 0.42)for protons of amide (-NH-CO-NH2) in compound [A4]. Signal at (2.46) proton of (N-CH-N) in diazepine ring, signal at and (4.54) proton of (NH2-CS-), signal and (2.98) proton of N(CH3)2 , two signal at and (6.71, 6.73) protons of alkene in diazepine ring (-CO-CH=CH-CO-), two signal at and (6.88 -7.65) for protons of phenyl rings in compound [A5] signal at and (2.95) proton of (N-CH-N) in diazepine ring, two signal at and (6.52 -7.67) protons of phenyl rings, two signal at and (6.02, 6.09) protons of alkene (CO-CH=CH-CO)in diazepine ring, signal at and (2.54) for protons of N(CH3)2 , signal at and (3.83) proton of amine (-NH-) in four membered cycle , at and (3.01) protons of methylene in (-C=N-CH2-NH) in four membered cycle in compound [A6]. Signal at and (3.39) of (N-CH-N) proton of diazepine ring, signal at and (2.47) protons of N(CH3)2 , two signal at  (1.82, 2.06) for triblete of (CH2- N) of azirine cycle, two signal at  (6.06, 6.18) of doublet signal (CO-CH=CH-CO) alkene in diazepine ring, two signal at (6.53, 7.94) of protons of phenyl ring(20 ,21)  in compound [A8]. Signal at (SH) thiol group, signal at (3.39) proton of (NH) amine at and (2.47)proton of N(CH3)2 , signal at  (2.06) proton of (N-CH-N), three signal and (1.82 , 1.74 , 1.37)proton of (-CH-CH2-) , two signal at  (6.53, 7.65) protons of phenyl rings in compound [A13]. Signal at (2.35) proton of N(CH3)2 , two signal at and (2.48, 2.54) for protons of (CO-CH2-CH2-CO) of cycles, threesignal at  (3.01, 2.95 , 2.85) for protons of (N-CH-CH2-S) of eight membered ring , two signal at (6.52, 7.67) for protons of phenyl ring in compound [A14]. Signal at  (3.01)proton of (N-CH-N) of imidazol one ring , two signal at and (3.38 , 3.01) for protons (N-CH-CH2-S) of thiazine ring , signal at  (2.48) for proton of N(CH3)2, two signal at (6.74, 7.67) for protons of phenyl rings in compound [A15]. Signal at (8.66) proton of imine group (CH=N)(20 ,21) , two signal at  (6.74, 7.66) protons of phenyl rings, signal at  (2.99) protons of N(CH3)2in compound [A17], all data are shown in Table (3) and figures (6-10).

 

(C.H.N)-Analysis:

(C.H.N)- Analysis, from compared the calculated with found data of these compounds, the results were comparable, the data of analysis, MF, names and melting points are listed in table (4).

 


 

 

Table (2) .FT.LR-data(cm-1) of compounds[1-20].

Others

(-CO-O-) of Lactone

(-CO-N-)

of Lactam

(C=N)

Imine group

Comp.

No.

ـــــــــــــــــــــــــــــ               

ــــــــــــ     

ــــــــــــ

1604

[1]

(C-NO2):1458 ,(N(CH3)2): 1284, (C-H aliphatic): 29,8

1714

1689

ـــــــــــ

[2]

(C-NO2): 13%, (N(CH3)2): 1284, (C-H aliphatic): 2929, (CH=CH): 3041, (NH2): 3425, 3367

ــــــــــــ

1691

ـــــــــــ

[3]

(N(CH3)2):1250, (CH=CH): 3100, (C-H aliphatic): 2933, (NH2): 3201, 3294

ــــــــــــ

1691

ـــــــــــ

[4]

(C-NO2): 1346, (N(CH3)2): 1298, (C-H aliphatic): 2999, (CH=CH): 3030, (NH2):3333, 3419, (C=S): 815

ــــــــــــ

1698

ـــــــــــ

[5]

(C-NO2):1355, (N(CH3)2): 1230, (C-H aliphatic): 2910, (CH=CH): 3030, (NH): 3282, (C=N) indo cycle of diazitedine Four membering

ــــــــــــ

1680

ـــــــــــ

[6]

(C-NO2): 1384, (N(CH3)2): 1250,(C-H aliphatic): 2929, (CH=CH): 3061, ((C=N) of ando cycle of Four membring): 1606

ــــــــــــ

1689

ـــــــــــ

[7]

(C-NO2): 1380, (N(CH3)2): 1280,(C-H aliphatic): 2897, (CH=CH): 3009, (C=S): 798

ــــــــــــ

1699

ـــــــــــ

[8]

(C-NO2): 1356 (N(CH3)2): 1225, (CH=CH): 3059, ( (NH) of amide):3304

ــــــــــــ

1672

ـــــــــــ

[9]

(N(CH3)2): 1284, (CH=CH): 3089,(C-H aliphatic): 2968, (NH of amide)=3321

ــــــــــــ

1689

ـــــــــــ

[10]

(N(CG3)2): 1240, (NH2): 3435,3421, ( (C=N)of indo cycle of melamine)=1588

ــــــــــــ

 

1618

[11]

(N(CH3)2): 2286, (SH): 2362, (C-H aliphatic): 2972, (NH2): 3230, 3365, (C=N) in docycl of melamine

ــــــــــــ

1675

ـــــــــــ

[12]

(N(CH3)2): 1246, (SH): 2362, (CH aliphatic): 2960, (NH2): 3340, 3281, ( (C=N) of indo cycle of melamine): 1600

ــــــــــــ

1695

ـــــــــــ

[13]

(N(CH3)2): 1240, (CH2-S): 1365, (C-H aliphatic): 2939, ( (C=N) indo cycle of melamine):1604

ــــــــــــ

1664

ـــــــــــ

[14]

(N(CH3)2): 1298, (CH2-S): 1398, (C-H aliphatic): 2939(C=N) indo cycle of melamine

ــــــــــــ

1681

ـــــــــــ

[15]

(N(CH3)2): 1294, (CH2-S): 1320, (C-H aliphatic): 2904(C=N) indo cycle of melamine

ــــــــــــ

1684

ـــــــــــ

[16]

(N(CH3)2): 1298, (C=N) of indo cycle of

melamine

ــــــــــــ 

ــــــــــــ

1624

[17]

(C+NO2): 1371, (N(CH3)2)=1255, (C-H aliphatic): 2904( (C=N) indo cycle of melamine): 1595, (C-O-C): 11, 5

ــــــــــــ

1688

ـــــــــــ

[18]

(N(CH3)2): 1230, (CH-S): 1431, ( (C=N) of indo cycle of melamine): 1608

ــــــــــــ

1680

ـــــــــــ

[19]

(N-(CH3)2): 1234, (NH): 3230, (C-H aliphatic): 2908( (C=N) indo cycle of melamine): 1597

ــــــــــــ

1662

ـــــــــــ

[20]

 

Table( 3 ). H.NMR(.ɓ. ppm) of Some Compounds.                                    

Other peaks

N(CH3)2

(N-CH-N) of alkene

(CO-CH=CH-CO) of alkene

Comp

No.

(8,66) proton of(Iminegroup) (6,74-7,66) proton of phenyl rings

(2,99)

ـــــــــ

ــــــــــ

[1]

(9,63) proton of oxazepine ring (O-CH-N), (6,74-7,66) proton of phenyl rings. 

(2,85)

ـــــــــ

(6,06) in oxazepine ring

[2]

(4,54)proton of (NH2-CS-), (6.88-7.65) proton of phenyl rings. 

(2,98)

(2,46)

(6,71,6,73) in diazepine ring

[5]

(1.82, 2.06) proton of (CH2-N) of azirine cycle, (6,53,7.94) protons of phenyl rings. 

(2,47)

(3,39)

(6,06,6,18) in diazepine ring

[8]

(9.63,10.42) protons of amide (-NH-CO-NH2), (6.74-7.65) protons of phenyl ring.

(2,99)

(2,47)

(2,25) in diazepine ring

[4]

(3.83) proton of amine(-NH-), (3.51) of (6.52-7.67) of phenyl rings.

(2,54)

(2,95)

(6,02,6,09) in diazepine

[6]

(5.91) of thiol group (SH), (3.39) of amine (NH), (1.82,1.74,1.37) of  (CH-CH2), (6.53-7.65)  phenyl rings.

(2,47)

(2,56)

ــــــــــ

[13]

(2.48,2.54) proton of (CO-CH2-CH2-CO), (6.52-7.67) proton of phenyl rings.

(2,35)

(3,88)

ــــــــــ

[14]

(3.38,3.51) proton of (N-CH-CH2-S), (3.51) proton of imidazolone (N-CH-N), (6.74-7.67) proton of phenyl rings.

(2,48)

ـــــــــ

ــــــــــ

[15]

(8.66) proton of Iimine group, (6.74-7.66) proton of phenyl rings.

(2,99)

ـــــــــ

ــــــــــ

[17]

 

Table (4). Physical properties and (C.H.N) analysis of compounds [1-20]          

 Found

M.P Co

M.F

Comp. No.

N %

H %

C %

15.113

5.268

66.120

159

C15H15N3O2

[1]

11.209

4.398

62.005

180

C19H17N3O5

[2]

20.349

4.651

58.574

208

C20H20N6O4

[3]

19.432

4.401

56.383

198

C20H20N6O5

[4]

16.156

4.313

56.154

204

C20H19N5O4S

[5]

19.795

4.582

59.813

206

C21H20N6O4

[6]

16.843

4.274

65.315

214

C27H22N6O4

[7]

15.291

4.294

58.265

182

C22H21N5O4S

[8]

17.314

3.603

55.105

234

C22H18N6O7

[9]

19.114

4.371

57.482

202

C21H20N6O5

[10]

38.011

5.246

55.558

359

C12H15N7

[11]

31.102

5.075

50.009

>360

C15H19N8OS

[12]

22.624

4.315

56.153

>360

C23H22N8O3S

[13]

18.342

4.126

53.303

260

C27H26N8O7S

[14]

18.482

29.917

54.016

222

C27H18N8O7S

[15]

20.416

4.574

59.518

240

C27H26N8O3S

[16]

24.020

6.068

69.121

>360

C30H33N9

[17]

18.115

3.147

35.086

>360

C51H39N15O18

[18]

13.352

4.593

65.891

>360

C51H45N9O3S3

[19]

22.887

6.106

64.071

>360

C39H45N12O3

[20]

 

Fig (1) .FT.IR- Spectra  of compound [4 ]

 

Fig (2) .FT.IR- Spectra  of compound [8 ]

 

Fig (3) .FT.IR- Spectra  of compound [ 11 ]

 

Fig (4) .FT.IR- Spectra  of compound [ 12 ]

 

Fig (5) .FT.IR- Spectra  of compound [ 17 ]

 

Fig (6) .1H.NMR- Spectra  of compound [ 2 ]

 

Fig (7) .1H.NMR- Spectra  of compound [ 10 ]

 

Fig (8) .1H.NMR- Spectra  of compound [ 12 ]

 

Fig (9) .1H.NMR- Spectra  of compound [ 13 ]

 

Fig (10) .1H.NMR- Spectra  of compound [ 19 ]

 

Fig(11): Chromatogram of comp.[2]

               

Fig(12): Chromatogram of comp.[9]   

 

Fig(13): Chromatogram of  Mixture[2-5 ,9]   

 

Fig(14): Chromatogram of comp.[5]     

 

Fig(15): Chromatogram of  comp.[4]   

 

Fig(16): Chromatogram of comp.[3]       

 

 


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Received on 05.07.2014         Modified on 20.07.2014

Accepted on 10.08.2014         © AJRC All right reserved

Asian J. Research Chem. 7(8): August 2014; Page 734-747